First appearance

Voiced by

Bobby is a young go-getter—very mellow, hip, and easy-going. He used to play bass guitar for The Pretenders and he encourages the Springfield University students to call him by his first name. Bobby is also very much not a hard-nosed disciplinarian, but is willing to take the blame for being too strict if disciplinary issues arise at the university. In fact, Bobby had never expelled anybody from school, prior to kicking out Benjamin, Doug and Gary for kidnapping Sir Oinks-A-Lot. Even then, Bobby only did it because of the influence of the pig's powerful friends (such as Richard Nixon).

In spite of Bobby's positive qualities, Homer Simpson takes an instant dislike to him, and spends most of his time at Springfield University nurturing an unreasonable resentment for the dean. Due to watching bad college comedy movies such as School of Hard Knockers, Homer has a stereotypical image of a college dean as an inflexible old fuddy-duddy. This persists in Bobby's case, even though Homer is several years older than Bobby.

But when Homer becomes remorseful for his part in getting the nerds expelled while he himself got off scot-free, he confesses everything to the dean: kidnapping Sir Oinks-A-Lot, hitting the dean with his car (in a gone-awry scheme to get the nerds re-admitted to school), and the other pranks he and the nerds pulled. Bobby, for his part, concedes that he may have been "a bit of an ogre" and rescinds the nerds' expulsions, although as a result of being hit by Homer's car, he apparently needed a new hip, given what Dr. Hibbert mentioned. After that, Bobby and Homer get along reasonably well, partying together and even teaming up to prank Richard Nixon and Springfield A&M.

After Homer's time at college, Bobby is present at a man's execution[1]. At some point afterwards, during Homer's college reunion, Homer decided to pull a prank on Dean Peterson involving a bucket with glue on the bottom and an ajar door as revenge for forcing him to donate. However, the plan backfired when it turned out that someone else set up the prank bucket, causing it to fall on Homer's head.[2]